Highroller54,
Not sure if you'd made a choice/purchase yet? I'm new to Harley's in general - but have ridden a number of various cruiser style motorcycles. Prior to buying my 2008 FXSTSSE2 softail springer, I have never owned a Harley or Springer bike.
When I was looking to buy a new bike, I took a really long time to check out the Harley landscape. I rode 17 different bikes in 12 months. Some as one and multi day rentals, others as quick dealer/private seller demo rides.
I also had the chance to ride all three of the FXSTSSE model year Springer bikes. Please note these are "handling" characteristics in respect to how I prefer to ride a bike, and others have different opinions of the handling characteristics. Here are my notes:
* 2007 - the 21" front wheel and slightly slacker head tube angle make for a "lazy" steering feeling - to me it felt like the bike kept trying to "sit up" when cornering, and I'd have to push it back down, however, initial steering response was relatively quick and agile
* 2008 - the smaller 18" front wheel, 200 mm rear, and slightly steeper (IIRC, about 1.5 degrees) head tube make this bike handle very quickly, and when pushed down in to a corner, she stays down and eagerly carves the corner and holds her angle
* 2009 - no changes to the front fork/rake angle (IIRC), but the rear goes from the 200mm wide to 240mm wide - this is similar to the "breakout" configuration - I find that the bike is a lot harder to corner due to the big fat 240mm rear - the "shoulder" of the rear tire doesn't "get over the hump" as easily, and you have to really push the bike hard in to a corner to get the same turning radius on a narrower width rear tire
I personally ride very hard, and very aggressively. Somewhat at odds with the "laid back cruiser" look/style. So for me - ultimately performance and good aggressive handling were important.
In general - I found all of the Softail models I rode (5 in total) to have the best handling characteristics and weight/balance/ride height for me. I also rode several Glide models (Wide, Super, etc), Road Kings, Softail Heritage, Softail Classic, Sportster 1200, Iron 883, Breakout, Fat Boy, Low Boy, etc... I kept notes on the handling of each bike, and felt like for my riding style - the 2008 FXSTSSE2 was by far the best bike.
For the ride characteristics of the Springer .... I hear a lot of people on this forum say that it's "firmer" - but to me, my Springer fork is softer and seems to more actively work than a standard fork. I do get pretty significant brake dive - which I'm looking at replacing the front shock absorber to correct. Not sure if it's an issue with my bike - or an issue with my perceptions of the Springer front end -vs- a standard fork?
I'm also a fairly big guy (6'3" and 220 lbs) - so my mass may play a part in it ... plus I ride two-up fairly often w/ the GF - and even though she's not heavy (very neatly proportionate, I'd say - but won't share her weight, since ... well, you probably understand why) ... we are right at the full weight limit on the bike (1150 pounds) with the accesories/addons/saddlebags/travel gear/etc...